100 Reasons To Love You
by demonoidphenomenom
Summary: "The moment he laid eyes on her, she was all that mattered to him. That was the beginning of something fascinating. The start of something punishing. He got a taste of that poisonous drip of love. And it was going to kill him.. Eventually." Dean/OFC
1. Dreamer

**FULL SUMMARY: 100 Reasons to love you is m****ainly based on Dean and his "Perfect Little Dream". He fantasizes about having a normal life, dealing with bills, kids, a wife, car payments, an actual job. When Dean meets Emma, A beautiful 24 year old from Northern Pennsylvania, He ends up falling for her. Once he realizes what has happened, He pushes her away as best as he can. But love has overcame him and he can't resist her anymore. Emma then tags along with the boys and journeys with them through all the horrible jobs they do. Dean knows this little fling of theirs can't keep going. When Emma brings him unplanned news, Dean doesn't know what to do. He becomes upset with himself, causing him to drink his life away. He only wanted a normal life..**

**This is my first attempt at a Supernatural Fiction.. Hope you guys like it :)**

**100 Reasons To Love You**

**Chapter 1: Dreamer**

A cold breeze approached Dean as he was walking back to the motel. It was nearing midnight. He had been gone for over 5 hours. Sam had to be out looking for him or he would be passed out from doing too much 'homework'. A total of 50 missed calls,27 voicemails, and 35 unread messages all from Sammy. Dean only went on walks like this when he was either pissed or just needed some time to think about some situation that had happened or what's going to happen. Trying to decide if he should go back or stay out longer, Dean stood in front of the liquor store, staring blankly at the blinking "Yes! We are open!" sign. He stood there for a good ten minutes and decided to get a case of beer. '6 pack should do..' He thought. A scraggly guy, close to his 60s, worked the cash register. Dean didn't feel up to conversing with anybody and just kept everything at a simple 'Hello and Have a good night.' He left the liquor store satisfied with his purchase.

He carried the 6 pack tightly cuffed in his hand. He headed towards the nearby playground that seemed old and rusted. He thought it was strange that a playground was near a liquor store. 'Perfect for pedos..' He shuttered at the thought and sat down on the bench. It was the middle of fall. It wasn't too warm or too cold. Almost like spring weather but a bit more colder. He quickly grabbed a bottle from the pack, opening it and then attempting to throw the lid in the trashcan. He failed that time and thought about picking it up before he left. He would end up forgetting about it by then. He stretched his legs out and placed his lips over the opening of the bottle and took a sip. He didn't think he was that thirsty after seeing he drank half of it within the first sip. He shrugged and took another sip but not as long as the first.

He stared up at the night sky, wondering about his life. He wasn't all that happy about it. He and his brother had been hunting ghosts, demons, and ghoulish monsters all their lives. So no, it wasn't perfect or all that nice. Dean didn't want this life. He wanted a life filled with love and happiness. A few kids and a good wife to come home to after a long day at work. They would have dinner together and argue about silly things. He wanted friends to watch football games with. He would take his family to the zoo or spend a day at the park. Cookouts, birthday parties, weddings, graduations.. He wanted all of that. But the life he has now, bites him in the ass every single day. He's died more than once, he's been to Hell and Heaven, He has an Angel for a best friend, and he deals with his brothers stupid decisions. His life was rather strange. No woman would want to settle with him if he ever told one what he actually does for a living.

Dean sighed and took one last swig of his beer before opening another one. All he can do is just dream about that normal life of his. He's never going to have it. As bad as it killed him to wish something so foolish. 'One day, You'll have it.. Just one day.' He thought and finished off his second beer. Tonight, he would drink away his dreams and worries and act as if he had never even thought about them. After all, he was a hunter with a cruel, heartbreaking dream.

Sammy almost gave up on finding Dean. He didn't know the town that well and asked around if anybody had seen him. He eventually found the liquor store Dean was at. The guy working that night said he did see him and that he headed towards the playground across the street. Sam thanked the guy and quickly left. He saw Dean laying on the park bench, humming one of his favorite songs. Sam let a deep breath out and walked over to him.

"Dean.." Sam said, nudging his drunken brother. Dean looked up at him and smiled.

"FINALLY!" He yelled, jumping up. His back cracked. "This bench is killing me.."

"You're drunk." Sam stated. Dean shook his head. "C'mon, let's get you back." Sam placed his hand on Dean's shoulder before walking towards the car. Dean frowned and followed his beanstalk brother. He treaded over his feet a couple times but made it back to the car in one piece. Sam started the car and the purr of the engine made Dean tingly. He loved that car, the car his Father gave him.

"It never gets old.." Dean smiled and hopped in the passenger seat. Sam had a irritated look on his face.

"You do realize we have to get up early tomorrow, right?" He said relentlessly. Dean looked at his brother, squinted his eyes, and broadened his shoulders.

"Yes, Sammy, I do know we have to get up early tomorrow." He replied back. "And I also know that you're getting on my nerves."

"Dean-"

"Sammy, just shut up. I don't need to hear you nagging about this, that and the other. I am frustrated so do me a favor and just drive back to the room." Dean said. Sam tightened his lips together and just left his brother alone. Something was bothering him really bad. He would ask Dean about it tomorrow when he had sleep and was in a better mood. Sam put the car into drive and headed back to the room. He was going to stop and get Dean a cheeseburger but didn't after seeing he had already passed out. Reality wasn't quite back yet. Dean dreamt of that perfect little life of his that night. For once, Dreaming actually meant _something_ to him.

**Well, that's that. PLEASE send me reviews! I want to hear your feedback on this and if I should continue.. Thanks for reading!**


	2. Emma

**Chapter 2: Emma**

Dean had awoken from his deep sleep the next day. The buzzing of the alarm clock irked him. His head was pounding and he had a hard on from his previous promiscuous dream. Sam was no where to be found. 'Probably getting food..' Dean thought. He quickly reached over and turned the alarm off. His hard on slowly went away. It's been quite some time since he's slept with a woman. The last time he fucked one was 2 months ago in Las Vegas. Her name was Holly. Long brown hair, hazel eyes, olive skin, a nice sized rack. Of course it was a one-nighter. He was gone the next day so it was never a really hard goodbye. Only a 'It was nice meeting you and thanks for the sex' kind of goodbye. He never allowed himself to get too close to any one. It wouldn't be a happy ending if he did. Dean finally managed to get out of bed. He stretched out his legs and arms, feeling ten times better. His headache was still killing him. He picked up his phone off the nightstand and looked to see if Sammy called or anything. Nothing. He decided to call Sammy anyways to find out where he was. He began calling him when Sam walked through the door. Dean hurried up and closed his phone.

"Where'd you go?" Dean asked, setting his phone back down.

"I went and put gas in the car.." Sam said, he took his jacket off and placed it over the back of the chair. "It was on empty when we had gotten back last night." Dean almost forgot about what happened last night. He raised his eyebrows. "We could have done that when we left this hell hole." He said, walking into the bathroom. Sammy sat down on the bed and waited for his brother. Not only did he get gas, He made a little stop outside of the little town they were currently in for a little down time. Fort Wayne, Indiana. Home of the famous Embassy Theater. They had taken care of some "Ghostly Business" that was threatening the lives of people who were related to the owner of the theater back in 1928. But that's taken care of and now they can head to Scranton, Pennsylvania for their next job. They had possible leads on a shape shifter.

"Hurry up, Dean!" Sam yelled for him. "We were suppose to be on the road by 7:30. It's almost 8." He began throwing most of his stuff into his bag. Dean walked out of the bathroom.

"Why such the rush, Sammy?" Dean said, smirking. "It's gonna take us a while to get there." He replied, rolling his eyes at Dean.

"I saw that." Dean said as he picked up his jeans off the floor. He looked at them a quick second. 'I only wore them yesterday.. They aren't _that _dirty..' He thought. He quickly put them on.

"Do we have any aspirin?" He asked Sam.

"No, Why?"

"Hangover." Dean said. Sam chuckled.

By the time they got everything together and out in the car, it was close to 8:30. They wouldn't be in Scranton, PA until about 6 if they drove straight through. That won't happen. Dean needed his food and of course piss breaks. That would add on another hour or so. Dean has always loved being on the road. He couldn't stay in one place for too long. Although, it would be nice to have a break from everything every once in a while. And that's where the walks and the occasional drinking away worries come in hand. Him and Sam would have a few drinks after a job or have some when they would relax at the motel. That never really helped him feel numb. Whenever he feels down about his life, he always has a way out. Drifting off into a different realm, a realm of infinite dreaming. He never leaves that place. He's _always _dreaming. Drinking always helps him get lost in that little dream world of his. Sam has caught him a few times drifting off into space but he never disturbed him. The only time he doesn't dream, is when he's on a job or doing research. Dean wasn't paying much attention to Sam. Just a few nods and a "Yeah, Okay." Sam knew he wasn't paying attention at all. He stopped talking about the job that was about to come and began reading a book that he had picked up at the library. He wasn't going to return it. He never returned library books. In fact, after he read them, he left them at Bobby's place for him to read. The books he collected were always on the paranormal or ancient myths. The typical topic of most human beings. Whether they believed in all of it or not, it's _all _real.

A few people have gone into mental institutes after seeing the truth on actual monsters. Big Foot, The Abominable Snowman, Lochness Monster.. They're all fake, made up creatures. All of that is a crock of shit. What Sam and Dean really do is real. Demons and Ghosts, Shape Shifters and Wendigos, Werewolves and Vampires, Djinns and Changelings. That's all true horror story shit. Dean wished none of that existed. His life would be a thousand times better if he didn't have to stress over crap like that.

"How much longer do we have?" Dean asked, yawning. He needed some coffee. The last stop they made was 4 hours ago.

"At least 30 minutes." Sam said, looking at the map. "The next exit isn't for another 15 miles." Dean was getting irritated. He wanted to get this over with.

"And then we'll be in Scranton?" He asked, Sam nodded. "Once we get a room, I'm going to head over to the Dennisons' House. You coming with?" Sam asked him.

"Nah, I'm just gonna hang back and try to get some sleep. I have a feeling this job is going to be a pain in the ass."

Dean was right. This job, or any job at that, is a pain in the ass. They're always getting hurt one way or another. If it be a broken or a severe cut to the arm. Bruises and scrapes. Good thing they knew how to take care of such injuries. They're lucky they're even _still _alive. They both died one too many times and always came back. The world would truly come to an end if they never came back from the dead. One couldn't live without the other. They're two inseparable brothers. No matter how many times they argue or get into fist fights, they love each other. Dean's always taking care of Sammy. Trying to clean up after his stupid mistakes. Same goes for Sam. If Dean doesn't do something right, Sammy will try his best to take care of it. They have each others back, through hell and back.

While Sam was out doing his "investigating", Dean decided not to take a nap and explore his options around town. He didn't have his car and he was kind of disappointed but Sammy needed it more than he did. While on his little stroll, Dean came across a liquor store. It was pretty much right next to the motel they were staying at. He also found a few places to eat at. He couldn't wait to try one of their bacon cheeseburgers. Not very many places had extremely good burgers but he could tolerate them. It's one of his favorite things to eat. Along with some beer. That was like Heaven to him. He walked passed a few stores, nothing interesting. He decided to head back to the room after becoming bored with walking around. As he approached the "Bingo! Motel" he noticed this incredibly beautiful young woman getting out her bags from her car. She had medium length golden blonde hair, deep blue eyes, delicate curves. Her skin was almost like a pale-like color, She had a little bit of a tint to it which meant she was rarely out during the day. Dean was mesmerized by her. She was almost like an angel. Speaking of angels, Cas hasn't been around lately.. The last time Dean saw him was when he and Sam needed some Friendly Angel help. Angels aren't that friendly but they mean well. Dean saw the girl struggle with her bags and decided to go see if she needed help. He trotted across the parking lot and over to her.

"Excuse me, Miss. Do you need any help with those?" He asked her, smiling. He always gave his "I'm Available" smile to women. She looked at him and smiled back. 'Well, fuck me, She's even more gorgeous when she smiles.." Dean thought.

"Oh, Yes. Here, take this one." She said, handing him one of her heaviest bags. Dean politely took it from her.

"I'm Dean, by the way." He told her.

"Emma, Pleased to meet you." She replied back, smiling again. Dean felt like he was going to explode any moment. She was just too beautiful and he wanted to know more about her.

"So, Emma, What brings you to a place like this?" Dean asked. Emma seemed a bit shy but she made small talk with him.

"I stay here during the weekend for work." She said. They walked slowly across the parking.

"What kind of work do you do?" He asked.

"I actually work at the town library." She said. Dean noticed she wasn't up for talking and left it at that. They arrived at her room. It wasn't too far from where Dean and Sam's room was.

"Me and my brother are actually a few doors down from you." He said, placing her bag on the ground. "If you want, you can stop by some time and hang around with us." He gave a small smile to her.

"Thanks, I'll think about it." She said, opening the door to her room. "Well, Dean, It was nice meeting you.." She placed her smaller bag in her room and then picked her bigger bag. Dean couldn't leave her, He didn't want to. He just met this girl and he's already wanting to everything about her. He hasn't even thought about fucking her and that's not like Dean. Women were his top priority.

"Emma.. I really want you to come by." He told her. She gave him an irritated look.

"You aren't the first guy who's tried sleeping with me. And believe me, it's not happening. Ever." She said. 'This woman has temper.. I LIKE IT!' He thought.

"I said nothing about sleeping with you!" He yelled to her as she slammed the door in his face. He'll come back later. He's not giving up on this girl just yet. He'll do anything just to talk to her again. Dean slowly turned away and walked back to the room. Sammy wasn't back yet. Dean just laid around and drifted back into his dream world. But only this time, It wasn't about his perfect family. It was about Emma. He wanted to hold her, to love her, to marry her. He doesn't know anything about her and he's already becoming fascinated by this woman. One things for sure, He's never thought about a girl like this since high school.

**Well, that's end of this Chapter. I hope you guys enjoyed it! I know it's not perfect but it's getting there. PLEASE R&R! I love feedback! :)**


	3. It's Only 5 In The Morning

**Chapter 3: It's Only 5 In The Morning**

Dean kept tossing and turning throughout the night. He just couldn't get Emma off his mind. Everything about her drove him crazy and he just met her. He knows nothing of this girl. He's never felt this way about anyone. It was always about ass and titties. He did care for women because they are such delicate angels and no monster should ever lay his hands on a woman. Or possess one in that matter. But demons will be demons and brain fuck whatever they can get there hands on. It was 5 am and Dean was still awake. Sam was snoring away, blanket over his head. One of two things Dean could do. One, he could go knock on Emma's door. Or two, he could smack Sam in the head and make him stop snoring. That might make it easier for Dean. No, he wanted to see Emma.

He got out of bed, changed into his clothes from the previous day, grabbed his phone and the motel keys and left. What he was doing was beyond insane. He stopped at the room next to hers debating if he should knock on her door or not. It wasn't like him to get out of bed in the middle of the night and knock on some chick's door because he wanted to talk to her. He was going nuts over her. It was practically killing him inside. He sighed deeply and turned back around. As he did so, He heard a door open up behind him. He stopped for a moment and looked over his shoulder. Emma was standing in the door.

"Dean?" She asked. He felt a little hot; maybe it was just the weather. It couldn't be. It was the middle of fall. He slowly turned around.

"What are you doing out here this late?" She asked him, walking closer to him. His body got tingly. She was beautiful.

"I.. Uh.. I was walking." He quickly said. Maybe a bit too quickly. He began sweating, as she got closer to him. Emma raised her eyebrows.

"Oh, okay.. I thought I had heard some one knocking on my door." She said. Dean felt embarrassed. He was going to knock on her door but decided it wasn't a good time.

"I didn't see anyone walk by it.." He told her.

"Okay. Well, I'll see you later then." She said and turned back around. Dean didn't want her to leave.

"Hey, uh, Emma?" He said, he was beginning to get butterflies in his stomach.

"Yes?" She said, looking at him.

"I'm, uh, about to get some breakfast down at that diner. I-I was wondering if you would like to join me?" He shyly asked. Emma gave him a small smile.

"That would be nice.." She said. Dean's eyes lit up with excitement. "I'll just go put on some clothes and I'll meet you in the parking lot." She went back into her room and changed into something more appropriate. A gray t-shirt, jeans, and a black leather jacket to go over it. She reached into her over night bag and pulled a gun out of it. Some librarian she was. She stuffed the gun into her back pocket and left her room, turning her light off and putting the "Do Not Disturb" sign on her door. She was hiding something she didn't want _anyone_ to see.

Dean was already in the parking lot waiting for Emma. When she finally came out, Dean stared her down like some kind of hungry wolf. He wanted to be with her so _badly._

"S-So, you ready?" Dean asked. He felt his cheeks get warm. Emma looked at him with happiness plastered on her face.

"Yeah, let's go." She said. Dean opened up the passenger side of the impala and she got in. He was excited she was riding in the same car as him. It would probably be the closest he'll ever get to her for a while.

"Nice car," Emma said, looking at him. "What model is it?"

"1967 Chevy Impala." He said, turning the engine on. It gave a low purr. Dean felt even more excited as he drove off. It wasn't too bad of a drive. Just a mile or so down the road. They kept the conversation going, talking mainly about cars and how idiotic people are when it comes to driving classic cars. Dean was fascinating Emma. The way he would talk about his Father's car, how he smiled at her, or how he occasionally looked at her just to make eye contact with her. Dean was warming up to Emma more and more as they carried on their conversation at breakfast. Emma laughed at some joke Dean made about the waitress wearing too much make up. They were having such a good time, they lost track of time. Dean forgot to put the ringer on his phone and had over 20 miscalls from Sam.

"My brother keeps calling." Dean said. Emma looked disappointed.

"We should head back. I have to be at work by 10." She said. Dean felt his heart sink. He didn't want to leave just yet.

"Okay." He sadly said. Dean's feet dragged across the parking lot to his car as they left. Emma was already in the passenger seat of the car by the time Dean got to it. The atmosphere around them changed periodically. One moment they were happy and talking and the next it was a feeling of disappointment. Either of them wanted to leave. But they had places to be and people to see. They arrived back at the motel. Emma gave Dean a hug and thanked him for taking her out. They both agreed on seeing each other again but probably not until the morning to come. Emma went back to her room and Dean went to his. He felt nothing but happiness as he returned. Sam was sitting on the bed, watching TV.

"Where have you been?" Sam asked as Dean closed the door.

"I was out." Dean said, placing the keys on the nightstand.

"I called you like 80 times." Sam said.

"I know. I had my phone on silent." Dean replied back. A moment of silence entered the room. Sam studied his brother as Dean looked through some papers that were lying on the table. He seemed more relaxed and happier. A small smile laid perfectly on his lips.

"What's gotten into you?" Sam asked. Dean quickly looked at him and couldn't help but smile even bigger.

"I met someone." He told his little brother. Dean felt proud saying that.

"Is this another one night stand?" Sam asked. Dean raised his eyebrows at him.

"No.. This girl isn't like any other. And I'm not going to fuck this up." He felt proud of his answer.

"You do realize it's not going to be easy to have a girlfriend." Sam said.

"Yes, I do know, Sammy." Dean said. He sat down in the chair and thought about what his brother said. All that excitement that was built up, disappeared. Sam was right. It's not going to be easy. Dean didn't want to let go of Emma. But he couldn't just give up his job. Those Demons would find him sooner or later. He wanted to be with Emma and kill those fuck head monsters at the same time.

"What did you find out about Mr. Dennison?" Dean asked, changing the subject. He didn't want his hopes to be crushed just yet.

"It turns out Mr. Dennison never did kill those people. He was sitting at home watching the game with his son on the night the murders took place." Sam told him. Dean leaned back in his chair.

"Looks like we got a definite shape shifter on our hands then." He said and gave Sammy a smirk. He was ready to fuck shit up and especially with all this excitement built up inside of him. It was going to be tough but the fight is _worth_ it.


	4. Once A Hunter, Always A HunterPart 1

**Chapter 4: Once A Hunter, Always A Hunter(Part 1)**

As the next few days carried on, Dean and Emma became much more closer. They never got bored with one another. Sam worried about his brother. He was happy that Dean had found some one but it just wouldn't work out. Dean would always be on the road, killing monsters, worrying about Emma, the possibility of him dying and never coming back. Demons would find Emma and use her against Dean. He couldn't put her at risk. Sam had tried talking to Dean about it but Dean wouldn't hear it. He was falling for her harder than he expected. It wasn't like Dean to obsess over one girl or fall completely head over heels for one. Sam didn't know what else to do, they were leaving that evening. Dean wanted to stay an extra but they were risking it. They both knew they couldn't stay in one spot for long. Demons would eventually catch up to them, no matter how careful they were in covering up there tracks. Sam and Dean continuously argued that day. All because of how Dean didn't want to leave just yet.. And then the most stupidest idea clicked into his head. He wanted to ask Emma if she would like to go with them. Sam exploded at the thought of it. Emma just couldn't possibly go with them. She would get killed.

"Have you fucking lost it?" Sam yelled. Dean rolled his eyes. He knew Sam wasn't going to like his little idea.

"It's better than staying in one spot.. I wouldn't have Emma fight off whatever demons or monsters that we encounter in the first place. She could just stay back at the motel or go out and check out all the stores." Dean said. The younger Winchester was 2 seconds from punching his older brother right in the face. He couldn't believe Dean. He couldn't believe that his brother would come up with an idiotic idea.

"Emma couldn't handle the fact that you hunt monsters. She would think of you as some sort of freak or some kind of psycho who needs some serious attention." Sam said, trying to convince Dean out of his idea. Dean wasn't really paying attention to Sam, like usual. All he wanted to do was go see Emma.

"I've fallen for her, Sam." Dean told him. Sam already knew, he could tell his brother was in love. Sam sighed and tucked his hair behind his ears. He didn't know what else to do. He could call Bobby and have him talk some sense into Dean. Or just knock him out and pretty much kidnap him away from Scranton, leaving Emma without a word. That would probably kill Dean if he never got the chance to see her one last time. Sam placed his head in his hands. Silence filled the room quicker than a vampire attacking it's prey.

"I'm outta here." Dean said and left the room. Sam quickly picked up a vase off the dresser and threw it at the door. He was pissed at Dean. Dean knew better not to get a girl involved into this kind of life.

Dean saw Emma get into her car and was curious to where she was going. He decided to go for a small ride and follow her. He wasn't going to stalk her. The first turn she made, he would go the opposite. But the thing was, Emma knew Dean was following her. She wanted him to do so. He had no idea where she was going. She made a right, a left, another left and then a right. Dean told himself to go the opposite direction of her but he was lost. He didn't keep track of where they were going. He figured to keep following, hoping they would end up back in town. He was wrong. After the final turn, They were near some kind of abandoned farm house. A barn sat off to the left of the house. Emma got out of her car and smiled gently at Dean. He was confused. What was she doing? He got out and continued to follow her. Not a word was said between the two. Emma walked up the steps of the old house and carefully opened the door. She turned to face Dean and motioned for him to come in. The moment he stepped in, a foul smell of decaying bodies entered his nostrils. He quickly covered his nose with the collar of his jacket.

"Ugh! What is that smell?" Dean yelled. Emma didn't say anything. She was up to something. They moved deeper into the house, the smell worsened. They eventually came to a room that had a devil's trap right in the middle. A chair sat in the center of it. A small table was at the tip of the trap, holy water and a bible sat on top of it. Dean was confused.

"Em, What is this?" He asked her. She slowly turned towards him and gave him a small smile.

"I'm a hunter, Dean." She told him. Dean didn't know what to say. He was shocked but yet relieved at the same time. Little Miss Innocent Emma was a hunter. An experienced hunter, if that.

"I know you and your brother are hunters as well. I've heard so much about the two of you." She said. Dean looked at her and smiled. "This is the greatest thing I have yet heard." He told her. Emma folded her arms and sighed.

"I didn't think you would like me for what I do." She said.

"Baby, I could never hate you." He said. He didn't want to say I love you just yet. They weren't official yet. And Dean couldn't wait for the moment they could actually be together. His life was finally turning around. Not by much, but it was slowly piecing together.

**Sorry for the extreme wait and for the chapter being so short. Part 2 will shortly come. I hope you are enjoying this so far! Thanks for reading! PLEASE SEND REVIEWS! **


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